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Enantioseparation of nicotine alkaloids in cigarettes by CE using sulfated β ‐CD as a chiral selector and a capillary coated with amino groups
Author(s) -
Kodama Shuji,
Morikawa Atsushi,
Nakagomi Kazuya,
Yamamoto Atsushi,
Sato Atsushi,
Suzuki Kentaro,
Yamashita Tomohisa,
Kemmei Tomoko,
Taga Atsushi
Publication year - 2009
Publication title -
electrophoresis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.666
H-Index - 158
eISSN - 1522-2683
pISSN - 0173-0835
DOI - 10.1002/elps.200800340
Subject(s) - nornicotine , chemistry , anabasine , sulfation , chromatography , cationic polymerization , nicotine , cotinine , capillary electrophoresis , alkaloid , amino acid , stereochemistry , nuclear chemistry , organic chemistry , biochemistry , neuroscience , biology
Nicotine (NC) and its related compounds (cotinine (CN), nornicotine (NN), anatabine (AT) and anabasine (AB)) were simultaneously enantioseparated by CE using a capillary with amino groups and sulfated β ‐CD as a chiral selector. The optimum running conditions were found to be 30 mM acetate buffer (pH 5.0) containing 8% sulfated β ‐CD with an applied voltage of +15 kV at 30°C using direct detection at 260 nm. Using a capillary coated with amino groups, the EOF migrates toward the positive pole. However, when sulfated β ‐CD was added to the BGE, it was found that the EOF migrated toward the negative pole due to ionic adsorption of sulfated β ‐CD to amino groups on the capillary inner wall. All the cationic analytes migrated as anions, suggesting that they formed stable anionic complexes with sulfated β ‐CD. With this system and a simple pretreatment with mini‐cartridges, NC alkaloids in five cigarette samples were enantioseparated. As a result, each of the compounds except for CN was detected. In the case of NC, only ( S )‐NC was detected (more than 99.9%), but in the case of NN, AT and AB, the ratios of ( S )‐isomer to total isomers were in the ranges 58–70, 81–85 and 59–65%, respectively. On the other hand, only NC was detected in cigarette smoke and the ratio of ( S )‐ and ( R )‐NCs was 96:4. The amounts of NC alkaloids in cigarettes suggest that the production of ( R )‐NC resulted from racemization due to the high temperature/burning of the cigarette.